After his football career ended, Rewald became president of a sporting goods store in Wisconsin called College Athletic and expanded the business across Illinois, Minnesota and Ohio before selling the franchise and moving to Hawaii with his wife and five children.[2]:43

In 1978 Rewald established an investment firm in Hawaii called "Bishop, Baldwin, Rewald, Dillingham and Wong".[7] The firm's name incorporated the names of Rewald and his partner Sunlin Wong along with the names of three prominent kama'aina who had no connection with the business: Charles Reed Bishop, Henry Alexander Baldwin and Benjamin Dillingham.[7] The firm claimed that funds were guaranteed by the Federal Deposit Insurance Corporation up to $150,000 and that minimum returns of 20% annually were guaranteed.[8] (As the firm was not a chartered bank it was not eligible for FDIC insurance.)

In 1983, the Internal Revenue Service began an investigation of Rewald when his firm's false FDIC insurance claims were discovered.[9] On July 29, 1983, Rewald attempted suicide at the Sheraton Waikiki Hotel, allegedly because the media was on the verge of exposing his background.[9] Six days later, the company was forced into bankruptcy.[1] Rewald was arrested on August 8, 1983, immediately after his release from the hospital, and was charged with theft by deception. He was held in lieu of $10 million bail.[9] He faced 98 charges and a maximum of 400 years in prison.[1] Sunlin Wong pleaded guilty and was sentenced to two years imprisonment.[1]

In reality, the investment firm had been a Ponzi scheme.[10] Rewald used money from new investors to pay interest to earlier investors, all the while siphoning off funds to pay for his lavish lifestyle.[9]

In addition to its Hawaii operation, the firm had also opened a branch in Auckland, New Zealand sometime in the 1980s. New Zealand television reports have suggested that Rewald or his firm was involved in the Māori loan affair of 1986–87.[11]

Rewald presented a surprising defense, claiming that his business had been a front for the Central Intelligence Agency.[1] Rewald claims that he was working for the CIA at the time and that the firm was set up by the CIA to serve as a cover for himself and 22 other CIA agents.[2]:68 Rewald claims that his work done at Bishop, Baldwin, Rewald, Dillingham and Wong and his lavish lifestyle were all part of his CIA cover and allowed him to gather national intelligence.[2]:68

In September 1984, ABC News broadcast a two-part investigation supporting his claims.[12] The CIA denied any connection and filed a formal complaint with the Federal Communications Commission (FCC).[12] Rewald did present substantial evidence of the CIA connection[7] and, at the CIA's request, all documents from the federal proceeding against Rewald were sealed on national security grounds.[12]

Rewald's trial lasted for eleven weeks in 1985.[1] 140 witnesses were called, including Jack Lord, who admitted to knowing Rewald but denied that he was employed as a consultant.[13] Rewald was convicted and sentenced to 80 years in prison.[10]